N,N,N',N'-Tetramethylethylenediamine → HCID 59215267, compound

HRID 2244833Notes

Reaction equation

HRID 2244833 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][O:9]2)=[C:4]([C:13]#[C:14][CH:15]2[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][CH3:23])[CH2:17][CH2:16]2)[C:3]=1[OH:24].CN(CCN(C)C)C.C([Zn]CC)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][O:9]2)=[C:4]2[CH:13]=[C:14]([CH:15]3[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][CH3:23])[CH2:17][CH2:16]3)[O:24][C:3]=12

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 25517Ammonium ChlorideHCID 59215253HCID 59215253, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 59215267HCID 59215267, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.80 g (17.3 mmol) of 7,8-difluoro-5-(4-propylcyclohexylethynyl)chroman-6-ol are initially introduced together with 0.26 ml (1.73 mmol) of TMEDA, and 9.6 ml (9.6 mmol) of diethylzinc (1 M soln. in heptane) are added to the mixture at 3° C. When the evolution of gas has subsided, 25 ml of toluene are added, and the batch is refluxed for 40 h. The solution is added to sat. ammonium chloride soln., and the mixture is extracted with toluene. The combined organic phases are washed with water and sat. sodium chloride soln. and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, 1-chlorobutane:pentane=2:1). Further purification is carried out by repeated recrystallisation from ethanol at reduced temperature, giving 4,5-difluoro-2-(4-propylcyclohexyl)-8,9-dihydro-7H-furo[3,2-f]chromene as a colourless solid having a melting point of 89° C. (Δ∈=−5.0).

Workup

  1. additionare added to the mixture at 3° C
  2. temperaturethe batch is refluxed for 40 h
  3. extraction, and the mixture is extracted with toluene
  4. washThe combined organic phases are washed with water and sat. sodium chloride soln
  5. customand dried
  6. concentrationThe solution is concentrated to dryness
  7. customthe residue is purified by column chromatography (SiO2, 1-chlorobutane:pentane=2:1)
  8. customFurther purification
  9. customrecrystallisation from ethanol at reduced temperature

Sources & evidence

ORD record
ord-1adbf8b2de564f7ebc31e12f61d36a30
Source dataset
uspto-grants-2010_03
Patent number
US07678929B2

Reaction notes

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